Sergey Brin: Vibram FiveFingers Classic

While Brin — the cofounder of Google and president of its parent company, Alphabet — doesn't exactly have stylish taste in shoes, he certainly has unusual taste. Brin has been known to wear Crocs for public appearances, but his msot serious fashion faux pas is his preference for Vibram FiveFingers, the wacky, sock-like shoes that have space for each of your individual toes.

Price: $75